Boss is an American smasher from Washington, D.C., currently residing in Falls Church, Virginia. A few months after Brawl was released, Boss started to compete in tournaments as Luigi and Mario. In doubles, he has teamed with many players, such as NinjaLink (R.O.B. and Pikachu), Logic (Olimar), Candy (Snake) and Anti (Meta Knight), reaching notable tournament placings such as 7th at Apex 2010 and 3rd at SKTAR. Boss is well known for his contributions to Mario and Luigi's metagames, being considered the best player of these characters in the world, and for taking matches off some of the best Brawl players in the world. Boss also plays with Dr. Mario at Melee and is considered to be one of the best Diddy Kong and Mario players in Project M. He is also considered one of the best Luigi players in Smash 4. He was formerly ranked 9th, 10th, and 19th on the MD/VA Project M, Melee, and Smash 4 Power Rankings, respectively.

In 2015, Boss was the most dominant Smash 4 player in MD/VA and won the majority of tournaments that he entered.

Boss previously held the record for most Xanadu Smash 4 tournaments won, having earned 1st place in 28 Xanadu tournaments. This record was surpassed by WaDi in 2017.

Boss is fairly infamous for being a self-professed "businessman", where he'll mostly only enter tournaments he's confident he'll win money in, while avoiding those he finds to have too strong of competition. This has led to Boss not attending most nationals and never going to those that are far from the northeast, despite being a top-level player, and showing up unannounced at out-of-state locals with weaker competition, instead of going to a closer tournament with stronger competition. Although he never saved his winnings and spent it all within days.

Boss is also known for being an extremely stoic player, who rarely ever shows the slightest bit of emotion win or lose. The extreme disparity between Boss' complete lack of emotion and his opponents being vibrant and expressing shock is a point of humor for many viewers, in the various GIF's and videos featuring Boss.